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. Author manuscript; available in PMC: 2015 Jan 17.
Published in final edited form as: J Org Chem. 2013 Dec 20;79(2):759–768. doi: 10.1021/jo402680v

Scheme 5.

Scheme 5

A. Evaluation of the benzyloxycarbonyl (Cbz) as an alternative protecting group for the lysine side chain and validation of deprotection conditions. B. The S,S-tetrazine ring of 15 is partially reduced to the dihydro-S,S-tetrazine system 16 upon exposure to hydrogenolysis conditions.